Ethyl Acrylate → 2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

HRID 22286

Reaction equation

HRID 22286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14]CC)=O)=[CH:6]2.[H-].[Na+].[CH2:19]([O:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH3:20]>C1(C)C=CC=CC=1>[O:14]=[C:12]1[C:7]2=[CH:6][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=3[N:8]2[CH2:24][CH:23]1[C:22]([O:21][CH2:19][CH3:20])=[O:25]

Participants

5

Reactant 3

HCID 8821Ethyl Acrylate2×HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 24758Sodium hydride2×

Product 1

HCID 199278602,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of ethyl 5-methoxy-indole-2-carboxylate (30 g, 137 mmol) in 1.5 L of toluene under N2 was treated with sodium hydride (6.7 g of 60% in oil, 167 mmol) and ethylacrylate (16.3 ml, 150 mmol). The mixture was heated to reflux. After 3 hours (hr), additional ethyl acrylate (3 ml) and sodium hydride (3.3 g) were added. After a total of 8 hr, the starting material was consumed completely and the mixture was quenched with ethanol and treated with water and dilute HCl and methylene chloride. The organic layer was washed with brine, dried and concentrated to give 2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole, which was used directly in the next step.

Workup

  1. temperatureThe mixture was heated to reflux
  2. customAfter a total of 8 hr, the starting material was consumed completely
  3. customthe mixture was quenched with ethanol
  4. additiontreated with water and dilute HCl and methylene chloride
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae3267b8cb1e4db9854b509f3b09ea44
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Linked notes

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